CN103980102A - Synthesis of 2,4-dihydroxy-5-methyl acetophenone and derivative thereof and application of 2,4-dihydroxy-5-methyl acetophenone and derivative thereof as bactericides - Google Patents
Synthesis of 2,4-dihydroxy-5-methyl acetophenone and derivative thereof and application of 2,4-dihydroxy-5-methyl acetophenone and derivative thereof as bactericides Download PDFInfo
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- CN103980102A CN103980102A CN201410177356.2A CN201410177356A CN103980102A CN 103980102 A CN103980102 A CN 103980102A CN 201410177356 A CN201410177356 A CN 201410177356A CN 103980102 A CN103980102 A CN 103980102A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
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Abstract
The invention discloses a synthesis method of 2,4-dihydroxy-5-methyl acetophenone and a derivative thereof. The obtained 2,4-dihydroxy-5-methyl acetophenone and the derivative thereof have the general structural formula as shown in the specification, wherein R is ethyl, propyl, n-butyl, isobutyl, n-amyl or tert-amyl. The specific synthesis method comprises the steps of taking 2,4-dihydroxy benzaldehyde as a raw material, and carrying out reduction and a Friedel-Crafts acylation reaction to synthesize the product. Experiments prove that the 2,4-dihydroxy-5-methyl acetophenone and the derivative thereof have quite good bacteriostatic effects, have a relatively low IC50 value, and can be applied in preparing agricultural preparations for prevention and treatment of paddy rice blast, tomato gray mold, tomato early blight, apple rot disease and apple anthracnose.
Description
Technical field
The present invention relates to compound 2, synthesizing of 4-dihydroxyl-5-methyl acetophenone and derivative thereof, particularly utilizes sodium cyanoborohydride by 2; 4-Dihydroxy benzaldehyde is reduced to 2; 4-orcin, then prepare 2,4-dihydroxyl-5-methyl acetophenone and derivative thereof through friedel-crafts acylation.
Background technology
2,4-dihydroxyl-5-methyl-acetophenone is a fungic origin polyketone meta-bolites, has anti-fungal activity of plant pathogenic and cytotoxic activity, can be used as lead compound and carries out the synthetic of class natural product.Referring to Chinese patent application: the compound 2 that utilizes the separation of fermentative broth of brown pore fungus to prepare, methods and applications (the application number: 200910020963.7 and 201110213976.3) of 4-dihydroxyl-5-methyl-acetophenone, (Ma YT, et.al.Natural Products as Sources of New Fungicides (I): Synthesis and Antifungal Activity of Acetophenone Derivatives Against Phytopathogenic Fungi, Chemical Biology & Drug Design, 2013.81 (4): 545-552), Ma Yatuan, the synthetic and bioactivity research of novel acetophenone derivs, Ph D dissertation in 2012.
Less about 2,4-dihydroxyl-5-methyl-acetophenone synthetic method report, its difficult point is intermediate 2,4-orcin synthetic (Cai Mengshen, Wang Lanming. synthesizing of the different black soya bean element of carbon glycosides research-XXVI. analogue, chemical journal, 1990,48:1191-1198); (Morais A.A.; et.al.Synthesis of three natural1; 3-diarypropanes:Two revised structures; Phytochemistry; 1989.28 (1): 239-242) reported with 2; 4-resorcylic acid is raw material; after bromination and decarboxylation, a benzyl is as hydroxyl protecting group; react and obtain intermediate 2 by Grignard; 4-orcin; obtain 2,4-dihydroxyl-5-methyl-acetophenone with Fries rearrangement or Friedel – Crafts reaction again.This method route is long, severe reaction conditions, and yield is only 40%.Though these two sections of documents have been reported the intermediate of 2,4-dihydroxyl-5-methyl-acetophenone as synthetic, have no its relevant report as natural product and anti-fungal activity of plant pathogenic.
Summary of the invention
The defect or the deficiency that exist for prior art; the object of the invention is to; provide a kind of 2; the synthetic method of 4-dihydroxyl-5-methyl-acetophenone and derivative thereof; the method by change the length of acyl group carbochain obtain bacteriostatic activity higher 2; 4-dihydroxyl-5-methyl acetophenone and derivative thereof, i.e. a kind of novel class natural product microbiotic.
In order to realize above-mentioned task, the present invention takes following technical solution:
The synthetic method of a kind of 2,4-dihydroxyl-5-methyl acetophenone and derivative thereof, the method obtain 2, the general structure of 4-dihydroxyl-5-methyl acetophenone and derivative thereof is:
Wherein, R=ethyl, propyl group, normal-butyl, isobutyl-, n-pentyl or tertiary amyl;
It is characterized in that, concrete synthetic method is, by quantitative 2,4-Dihydroxy benzaldehyde obtains 2 with sodium cyanoborohydride reduction, 4-orcin, quantitative different fatty acid anhydrides are added in 2,4-orcin and boron trifluoride ether solution to 80 DEG C of backflows at 0 DEG C, after completing by TLC tracking detection reaction, reaction solution is cooled to room temperature, pours in mixture of ice and water, is extracted with ethyl acetate; Organic phase is used saturated sodium carbonate solution successively, saturated nacl aqueous solution washing, anhydrous sodium sulfate drying, concentrating under reduced pressure, its resistates, taking the sherwood oil of volume ratio 5:1 and the mixing solutions of ethyl acetate as eluent, by silica gel column chromatography separating purification, obtains 2,4-dihydroxyl-5-methyl acetophenone and derivative thereof, yield be 60% and more than.
Applicant is to above-mentioned 2, and 4-dihydroxyl-5 methyl-acetophenone and derivative thereof have carried out the test of bacteriostatic activity, adopt five kinds of pathogenic bacterias, and result shows, 2,4-dihydroxyl-5-methyl-acetophenone and derivative thereof have good fungistatic effect, and IC
50be worth lower.Can be used in the application of the disinfectant use in agriculture of preparation control rice blast, graw mold of tomato, early blight of tomato, canker of apple fruit, apple anthracnose.
Embodiment
According to technical scheme of the present invention, the synthetic method of 2,4-dihydroxyl-5-methyl acetophenone and derivative thereof, first prepares 2,4-orcin, and its structural formula is as follows:
Concrete synthetic method is: next step is synthetic in the existence of reductive agent sodium cyanoborohydride for 2,4-Dihydroxy benzaldehyde.Reaction formula is as follows:
Raw material 2,4-Dihydroxy benzaldehyde and reductive agent sodium cyanoborohydride mol ratio are 1:1.5, and temperature of reaction is 25 DEG C, and pH value is controlled at 3-4, and the reaction times is controlled at 3-4h.
Make 2,4-orcin is removed by product, obtains the product of purifying.The method of removing by product can adopt existing separating and purifying technology, and if underpressure distillation is except desolventizing, recrystallization, filters, and the method such as column chromatography for separation is carried out purifying.
In above-mentioned reaction, produce a small amount of HCN gas, so glycerol and alkali liquor absorption for tail gas.
Prepare 2,4-dihydroxyl-5-methyl acetophenone and derivative thereof, its structural formula general formula is as follows again:
Wherein, R=ethyl, propyl group, normal-butyl, isobutyl-, n-pentyl or tertiary amyl; Synthetic method is: 2,4-orcin Fu Shi catalyzer exist under through acylation reaction one-step synthesis.Reaction formula is as follows:
Wherein Fu Shi catalyzer is selected BF
3, raw material 2,4-orcin and catalyst B F
3molar ratio range is 1:4～1:5, raw material 2, and the molar ratio range of 4-orcin and acylating reagent acid anhydrides is 1:1～1:1.5, this reaction is first by 2,4-orcin and catalyst B F
3add in reaction flask, drip and slowly drip acid anhydrides under ice bath, drip off and be progressively warming up to 80～90 DEG C, the reaction times is controlled at 4～6h, yield be 60% and more than.
Make 2,4-dihydroxyl-5 methyl-acetophenone and derivative thereof are removed by product, obtain the product of purifying.The method of removing by product can adopt existing separating and purifying technology, and if underpressure distillation is except desolventizing, recrystallization, filters, and the method such as column chromatography for separation is carried out purifying.
The catalyst B F using in above-mentioned reaction
3facile hydrolysis generates boric acid, so will avoid there is water in system as far as possible.
Below the embodiment that contriver provides:
Embodiment 1:2, the preparation of 4-orcin
In the there-necked flask of 100ml that stirring and device for absorbing tail gas are housed, add 2 of 0.69g (5mmol), 4-Dihydroxy benzaldehyde, sodium cyanoborohydride 1g (15mmol), a small amount of tropeolin-D is done acidity indicator, in a 50ml constant pressure funnel, slowly drip 30ml tetrahydrofuran solution
It is yellow that reaction solution is.After dropwising, from another 25ml constant pressure funnel, slowly drip the 15ml1N HCl aqueous solution, make reaction solution keep orange.At 25 DEG C, react 3h.After reaction finishes, add 30ml distilled water, stir 10min, with extracted with diethyl ether (15ml3 time), separate organic phase, 50ml saturated sodium-chloride water solution washing 3 times for ether layer, anhydrous sodium sulfate drying.Underpressure distillation, except desolventizing, obtains producing thick thing, the sherwood oil taking volume ratio 5:1: the mixing solutions of ethyl acetate is eluent, by silica gel column chromatography separating purification, obtains 2,4-orcin, is white solid, fusing point: 103-104 DEG C, and yield is 90%.
Structural formula:
Molecular formula: C
7h
8o
2
1H?NMR(300MHz，CD
3OD)δ2.06(3H，s，CH
3)，6.20(1H，dd，J?＝2.0and8.8Hz，H-5)，6.28(1H，J＝2.0Hz。H-3)，6.84(1H，d，J＝8.8Hz，H-6)；EI-MS?m/z123.0524【M-1】
-。
Embodiment 2:2, the preparation of 4-dihydroxyl-5-methyl acetophenone (compound 2)
In the 50ml there-necked flask that whipping appts and reflux condensation mode are housed, add 0.31g (2.5mmol) 2,4-orcin, 1.5ml (12.5mmol) boron trifluoride ether solution, at 0 DEG C, slowly drip 0.35ml (3.75mmol) diacetyl oxide, drip off, progressively be warming up to 80 DEG C, stirring reaction 4h.After reaction finishes, reaction solution is cooled to room temperature, pour in 20ml mixture of ice and water, stir 15min, with 15ml ethyl acetate extraction 3 times, separating reaction liquid, ethyl acetate layer is used saturated sodium carbonate solution successively, saturated nacl aqueous solution washing, anhydrous magnesium sulfate drying, concentrating under reduced pressure, its resistates is taking the sherwood oil of volume ratio 5:1: the mixing solutions of ethyl acetate is as eluent, pass through silica gel column chromatography separating purification, obtaining 2,4-dihydroxyl-5-methyl acetophenone, is faint yellow look solid, fusing point: 168-169 DEG C, yield is 64%.
Structural formula:
Molecular formula: C
9h
10o
3
1H?NMR(500MHz，CD
3OD)δ2.00(3H，s，CH
3)，2.39(3H，s,COCH
3),6.12(1H，s，H-3),7.43(1H，s，H-6)。
13C?NMR(125MHz，CD
3OD)113.90(s，C-1)，164.75(s，C-2)，102.70(d，C-3)，164.55(s，C-4)，118.18(s，C-5)，134.14(d，C-6)，204.11(s，C-7)，26.23(q，C-8)，15.49(q，C-9)；EI-MS?m/z165.13【M-1】
-。
Embodiment 3:2, the preparation of 4-dihydroxyl-5-methyl phenyl ketone (compound 3)
Synthetic method is with embodiment 2 (acid anhydrides used is propionic anhydride).Obtain faint yellow solid, fusing point: 158-159 DEG C, yield is 65%.
Structural formula:
Molecular formula: C
10h
12o
3
1H?NMR(500MHz，CD
3OD)δ1.17(3H，t，C-CH
3),2.04(3H，s，CH
3)，2.92(2H，m，CH
2-CH
3)，6.39(1H，s，H-3)，7.55(1H，s，H-6)。
13C?NMR(125MHz，CD
3OD)112.00(s，C-1)，162.69(s，C-2)，106.47(d，C-3)，162.20(s，C-4)，110.90(s，C-5)，128.80(d，C-6)，205.70(s，C-7)，30.41(t，C-8)，7.72(q，C-9)，6.23(q，C-10)；EI-MS?m/z179.10【M-1】
-。
Embodiment 4:2, the preparation of 4-dihydroxyl-5-methylbenzene butanone (compound 4)
Synthetic method is with embodiment 2 (acid anhydrides used is butyryl oxide).Obtain faint yellow solid, fusing point: 137-138 DEG C, yield is 62%.
Structural formula:
Molecular formula: C
11h
14o
3
1H?NMR(500MHz，CD
3OD)δ0.98(3H，t，C-CH
3)，1.73(2H，m，C-CH
2-CH
3)，2.06(3H，s，CH
3)，2.93(2H，m，CH
2-CH
3)，6.51(1H，s，H-3)，7.65(1H，s，H-6)。
13C?NMR(125MHz，CD
3OD)112.58(s，C-1)，162.84(s，C-2)，106.80?(d，C-3)，161.94(s，C-4)，110.90(s，C-5)，129.34(d，C-6)，205.15(s，C-7)，39.19(t，C-8)，18.09(t，C-9)，13.20(q，C-10)，6.81(q，C-11)；EI-MS?m/z193.01【M-1】
-。
Embodiment 5:2, the preparation of 4-dihydroxyl-5-aminomethyl phenyl isobutyl ketone (compound 5)
Synthetic method is with embodiment 2 (acid anhydrides used is isobutyric anhydride).Obtain faint yellow solid, fusing point: 132-133 DEG C, yield is 60%.
Structural formula:
Molecular formula: C
11h
14o
3
1H?NMR(500MHz，CD
3OD)δ1.16-1.18(6H,d,C-(CH
3)
2)，2.07(3H，s，CH
3)，3.63(1H，m，CH-(CH
3)
2)，6.51(1H，s，H-3)，7.71(1H，s。H-6)。
13C?NMR(125MHz，CD
3OD)112.14(s，C-1)，164.74(s，C-2)，107.83(d，C-3)，162.99(s，C-4)，112.10(s，C-5)，130.02(d，C-6)，210.12(s，C-7)，34.95(d，C-8)，19.91(q，C-9，C-10)，7.77(q，C-11)；EI-MSm/z193.02【M-1】
-。
Embodiment 6:2, the preparation of 4-dihydroxyl-5-methylbenzene pentanone (compound 6)
Synthetic method is with embodiment 2 (acid anhydrides used is valeric anhydride).Obtain faint yellow solid, fusing point: 105-106 DEG C, yield is 62%.
Structural formula:
Molecular formula: C
12h
16o
3
1H?NMR(500MHz，CD
3OD)δ0.92(3H，t，CH
2-CH
3),1.39(2H，m，CH
2-(CH
2)-CH
3),1.67(2H，m，C-(CH
2)-CH
2)，2.06(3H，s，CH
3)，2.95(2H，t，CH
2-CH
2)，6.49(1H，s，H-3)，7.67(1H，s，H-6)。
13C?NMR(125MHz，CD
3OD)112.55(s，C-1)，163.22(s，C-2)，106.83(d，C-3)，162.84(s，C-4)，110.96(s，C-5)，129.54(d，C-6)，205.41(s，C-7)，37.08(t，C-8)，32.18(t，C-9)，26.95(t，C-10)，13.33(q，C-11)，6.82(q，C-12)；EI-MS?m/z207.04【M-1】
-。
Embodiment 7:2, the preparation of 4-dihydroxyl-5-aminomethyl phenyl trimethylammonium ethyl ketone (compound 7)
Synthetic method is with embodiment 2 (acid anhydrides used is trimethylacetic acid acid anhydride).Obtain faint yellow solid, fusing point: 136-137 DEG C, yield is 64%.
Structural formula:
Molecular formula: C
12h
16o
3
1H?NMR(500MHz，CD
3OD)δ1.41(9H，s,C-(CH
3)
3)，2.07(3H,s，CH
3)，6.48(1H，s，H-3)，7.90(1H，s，H-6)。
13C?NMR(125MHz，CD
3OD)111.49(s，C-1)，164.65(s，C-2)，105.95(d，C-3)，161.12(s，C-4)，110.32(s,C-5)，130.18(d，C-6)，210.56(s，C-7)，43.81(s，C-8)，28.33(q，C-9，C-10，C-11)，7.08(q，C-12)；EI-MS?m/z207.03【M-1】
-。
The mensuration of Fungicidally active
Growth velocity suppresses method the compound of synthesized is carried out to virulence and EC
50the mensuration of (μ g/mL).The pathogenic bacteria of test is isolated five kinds of pathogenic fungies from the Common Diseases of field, is respectively apple decay, apple anthrax, tomato early epidemic, tomato gray mould, paddy rice rice blast.
Implementation method is: under aseptic condition, the sample acetone soln preparing is mixed to the PDA substratum of thawing, make the concentration of this compound in substratum reach 100 μ g/mL, after condensation, inoculate above-mentioned pathogenic bacteria, each processing repeats 3 times, 28 DEG C of constant temperature culture, measure a pathogenic bacteria bacterial plaque diameter every 24h, until the bacterial plaque of blank covers with flat board.Positive control is for disliking mould spirit.The compound after primary dcreening operation, inhibiting rate being reached more than 80% carries out EC
50test, compound 2-7 is made into 100 μ g/mL successively, 50 μ g/mL, 25 μ g/mL, 12.5 μ g/mL, the band poison substratum of 6.25 μ g/mL series, positive control is for disliking mould spirit.Finally calculate its virulence according to the inhibiting rate of different concns, draw virulence equation and EC
50value.The results are shown in Table 1 and table 2.
Table 1: the inhibiting rate (100 μ g/mL) of compound 2-7 to five kinds of pathogenic bacterias
Table 2: virulence equation and the EC of compound 2-7
50(μ g/mL)
In sum, above-described embodiment prepare 2,4-dihydroxyl-5-methyl acetophenone and derivative thereof (compound 2-7) can be used in the agricultural bactericide application of preparation control plant pathogenic fungi.
Claims (2)
1. one kind 2, the synthetic method of 4-dihydroxyl-5-methyl acetophenone and derivative thereof, the method obtain 2, the general structure of 4-dihydroxyl-5-methyl acetophenone and derivative thereof is:
Wherein, R=ethyl, propyl group, normal-butyl, isobutyl-, n-pentyl or tertiary amyl;
It is characterized in that, concrete synthetic method is, by quantitative 2,4-Dihydroxy benzaldehyde obtains 2 with sodium cyanoborohydride reduction, 4-orcin, quantitative different fatty acid anhydrides are added in 2,4-orcin and boron trifluoride ether solution to 80 DEG C of backflows at 0 DEG C, after completing by TLC tracking detection reaction, reaction solution is cooled to room temperature, pours in mixture of ice and water, is extracted with ethyl acetate; Organic phase is used saturated sodium carbonate solution successively, saturated nacl aqueous solution washing, anhydrous sodium sulfate drying, concentrating under reduced pressure, its resistates, taking the sherwood oil of volume ratio 5:1 and the mixing solutions of ethyl acetate as eluent, by silica gel column chromatography separating purification, obtains 2,4-dihydroxyl-5-methyl acetophenone and derivative thereof, yield be 60% and more than.
2. described in claim 1, method obtains 2, and 4-dihydroxyl-5-methyl acetophenone and derivative thereof are for the preparation of the application of the disinfectant use in agriculture of control rice blast, graw mold of tomato, early blight of tomato, canker of apple fruit, apple anthracnose.
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| CN101492356A (en) * | 2009-01-19 | 2009-07-29 | 西北农林科技大学 | Method for separating and preparing compound 2, 4-dihydroxy-5-methyl-acetophenone by using fermentation liquor of Polyporus fuscus |
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| CN101492356A (en) * | 2009-01-19 | 2009-07-29 | 西北农林科技大学 | Method for separating and preparing compound 2, 4-dihydroxy-5-methyl-acetophenone by using fermentation liquor of Polyporus fuscus |
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| Title |
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| JUSTIN T. J. SPENCE ET AL.: "Biomimetic Total Synthesis of ent-Penilactone A and Penilactone B", 《ORGANIC LETTERS》, vol. 15, no. 15, 9 July 2013 (2013-07-09) * |
| LAN XIE ET AL.: "Anti-AIDS Agents. 42. Synthesis and Anti-HIV Activity of Disubstituted (3’R,4’R)-3’,4’-Di-O-(S)-camphanoyl-(+)-cis-khellactone Analogues", 《J. MED. CHEM.》, vol. 44, 12 January 2001 (2001-01-12), pages 664 - 671, XP002411671, DOI: 10.1021/jm000070g * |
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| JP2019001756A (en) * | 2017-06-16 | 2019-01-10 | 住友ベークライト株式会社 | Antifungal agent, antifungal resin film, antifungal laminate film, and antifungal package |
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